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Outlook 2010 dragging attachments appends extra extension

Question

We have a user who drags attachments from emails they've received into new messages. When they do this the attachment gets an extra extension appended to it e.g. 12345.pdf becomes 12345.pdf.pdf - this happens with any file type. If they then drag and
drop the appended file to another email, it get appended again.

Over the last couple of days we have been getting mail rejections. We use a Linux mail transport running Mailscanner which objects to double/triple/quadruple filename extensions. It is designed to stop mails that have attachments say....
filename.doc.exe which is a common trojan deployment method. It actually stops any double (or more) file extension. So when we started getting and sending mail with attachments with filename.doc.doc or filename.pdf.pdf.pdf.pdf Yes it
really did add four extensions! I had to find out why pretty quick. we send a lot of mail with invoices / orders/ statements attached and gradually more and more people in the companies were getting rejections. It took a while and we tried
blaming lots of programmes first (antivirus etc) but we eliminated everything.

Not to bore you with all the details of the tests I did, I did find out that It occurred when a user, had an attachment on an email they wished to email to someone else i.e. They would either drag & drop or copy and paste the attachment into a new mail.
At this point when pasted, the filename suddenly aquired a second extension. This is at the point of creation of the new mail, before even being sent. Not a problem if the attachment was saved off and then attached using insert, or if the original mail
was forwarded.

My machine was fine, as were some others. My machine had been nagging me for a couple of days to reboot after the latest MS updates. So I did reboot. Suddenly, I am now having the same problem as others. Even I could work out that
the only thing that had changed was the MS updates (ten in my case)

I took a clean machine, installed each update one by one starting with the Office ones. Testing after each install, then rebooting and testing again, then moving to the next update.

Suffice to say that as soon as I installed KB2687315 I could replicate the problem.

As soon as I removed KB2687315 the problem disappeared

We are seeing a lot of incoming mail being stopped as well as our outgoing so I think this could turn out to be a major problem!!

We always copy and paste attachments from one email to a new message we are composing but ever since a few days ago it's been duplicating the extension like fredquango says.

For example, if somebody sends me a file photo.jpg and I copy and paste that onto a new email it will change the file name to photo.jpg.jpg, and if I do it again it becomes photo.jpg.jpg.jpg and so on...

When I try sending a file without any extension it works on the first email, but when I go and copy it from that email and paste it onto a new email nothing happens, it doesn't attach the file.

We are having this problem on all of our computers, we are running Windows Vista and 7, they all have ESET Endpoint Antivirus installed but even with it disabled and with Outlook in safe mode we are still having this problem.

I just started having the same problem - same deal - must have just started a few days ago. Am running Windows Vista and Outlook 2010. I'll try a system restore and see if it is some Windows update causing it.

We just noticed this too. It seems to lead back to
KB2687315 (Office 2007) / KB2553488 (Office 2010). These are updates considered critical by
MS Security Bulletin 9 Oct 2012, so uninstalling them seems not that good an idea. They patch vulnerabilities in Word for which active exploits are in the wild.

We have discovered a workaround: if you drag the attachment into the attachment box of the new email no extra extension is added. Most likely because this is Outlook, and the email message itself
is edited in Word.

The attachment box is not present at first though, it appears only after dropping the first attachment. We now delete this attachment and drop the attachment again into the attachment box, and see: no extension added.

Wish I had seen this thread last week, I was beginning to think I was the only one who had noticed this problem!! I have another thread open here with a similar topic and threads elsewhere.

Some things I have found out so far:

A few mail checking programmes will reject any mail with a double/triple/quadruple extension (yes I have seen 4 extensions on a mail) In particular, because we use it, Mailscanner. It is rejecting both incoming and outgoing mail with these extra extensions.
Yes, it is possible to add a rule in the config to allow double extensions but why should I put my networks at risk because an ill designed update has changed the game.

Yes, you can remove the update on Windows 7 (in our case we use Office 2007 Pro across the Group due to legacy software requirements) and the problem stops immediately. BUT on some Windows XP machines the update KB2687315 will not remove.
A removal deletes the $uninstall folder from Windows folder, but does not actually remove or restore anything and once that $uninstall fodler is gone you are pretty stuffed at trying to rid your machine of the update. This laptop I am typing
this on has exactly that problem.

It is incredibly difficult to get to talk to anyone at Microsoft who can help (I am still trying through some contacts I have) Every phone call seems to lead to an Asian call centre where they will not / can not help if your product is not on the list in
front of them!

I know from talking to an engineer in the USA who works for a Mail hosting/processing company that he is seeing a major increase in traffic with multiple filename extensions since last Tuesday. Fortunately for one of my companies, they do not actually
stop mail with duplicate extensions, only double extensions such as .doc.exe

IdeActive's workaround does work. But does Microsoft seriously expect me to retrain all our users and possibly some clients and suppliers who are having the same problems, to get them out of their copy/paste drag/drop habits, and there are quite a few
that years ago would have been described as Data input clerks....if you get my drift.

This is getting ridiculous. I have now come across one of our users on a laptop, who can not only NOT drag & drop or copy and paste but cannot insert either.

When he saves an attachment that he has failed to send to a customer to his desktop using a correct filename (look at the properties of the file and it only has one extension) When he then opens a new mail, and inserts from the menu, the saved file it suddenly
appears with two extensions again!!

On this machine the only option still working is to open the file, then using the send to as attachment menu,this inserts the file properly into an email.

I've run into another attachment copy/paste issue that I've isolated down to KB2687315. For only certain messages, if the message item is copied from the mailbox view and pasted into a new message or calendar item, it will not paste as an attachment but
will instead paste the message data from the mailbox view along with the column headers:

This seems to be only for certain messages, while others will paste correctly as an attachment. Pasting directly into the attach field works properly though (as was noted in a previous response). Unfortunately that field is not always visible.

Addendum: upon further troubleshooting, I've narrowed this down to happening on messages that have the pound/hash/# symbol in their subjects. So far it doesn't occur on any others.

Is Microsoft aware of this issue? I can confirm that in my environment (desktops and laptops running Win7 Pro x64, Office 2007, iManage), I can apply the patch and run into the extension duplication issue when pasting attachments (the
extensions keep piling up the more you copy the attachment between emails).

This needs to be fixed ASAP, I don't like skipping security updates when exploits are in the wild.

As IDEActive pointed out, these particular updates are supposed to be "critical" So although removing the update in Windows 7 does solve the immediate problem, I would not recommend this as anything other than a temporary fix.

Enough people need to start shouting to get Microsoft to really fix this problem they have caused.

Let me add another vote for a better fix for this issue, and soon. There are all sorts of reasons why people need to drag attachments between e-mails. It seems clear that the recent critical security fixes have caused this artifact of duplicated extensions
e.g. "myfile.pdf.pdf" Obviously it's a bug, but as other posters have commented, some AV scanning will block messages with multiple extensions as historically these have been used to hide executable code.

Wow. Sign of the times I guess. With the exception of the the smaller shops, it seems hard to get a timely response via email. Best luck seems to be had in support forums. If I can't find any updated info about this info by Monday,
I'll consider placing a call with them. It's a bug so I shouldn't have to worry about cashing in a support credit/voucher (I forget how that works, I just call if I need help and that's a rare event).

We had an issue where we could not copy attachments from one email to another email (or drag/drop) if the attachment file name had a pound/hash/number sign (#). Uninstalling KB2553488 seems to have resolved it for now.

Thanks to the moderator for merging the two threads about this problem together. As i have been posting in both, I will try to find time to go through and delete my duplicate posts (so it is easier to read the whole thread)

Our users have just noticed this problem happening. We are running Windows 7 x64 sp1 and Outlook 2010, not really keen on removing a security update. Microsoft pls could you give us a time scale as to when a fix will be released for this? very
annoying for the users.

KB2782404 (Attachment file extension is duplicated when added to email in Outlook 2007 and Outlook 2010) describes this issue and includes a link to a related hotfix --
http://support.microsoft.com/kb/2782404

I have just downloaded and installed the Hotfix on my system. I confirm it fixes the attachment extension being duplicated.

Is Microsoft going to release a fix for this via Windows Update in the near future? I hope so. If not, can you make a .msi version of this Hotfix so that I can distribute it via GPO? I don't have any way to distribute a .exe automatically.

I have just downloaded and installed the Hotfix on my system. I confirm it fixes the attachment extension being duplicated.

Is Microsoft going to release a fix for this via Windows Update in the near future? I hope so. If not, can you make a .msi version of this Hotfix so that I can distribute it via GPO? I don't have any way to distribute a .exe automatically.

I can't speak to the plans for release plans for this hotfix with regard to Windows Update, but I can tell you how to extract the MSP file from the hotfix executable and use an msiexec command line to install it.

1) Download the appropriate hotfix via the links in KB2782404.

2) Extract the contents of the downloaded hotfix executable to a temporary folder, using a command line similar to the following (references to "C:\KB2687556" and "C:\KB2687556\extracted" are examples which can be changed to match your environment):

3) Use command lines similar to the following to silently install the updates using the Wndows Installer and create a related verbose log file in the temp directory. Change "/QN" to "/QB" for an installation with only a basic progress indicator (references
to "C:\KB2687556", "C:\KB2687556\extracted", and log file names are examples which can be changed to match your environment):

It seems that KB2687556 fixed our Outlook file attachment copy/paste from existing e-mail to new e-mail issue as well. Files with the "#", or hash tag, pound symbol, can now be dragged/dropped or copy/pasted without any issues.

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